organic compounds\(\def\hfill{\hskip 5em}\def\hfil{\hskip 3em}\def\eqno#1{\hfil {#1}}\)

Journal logoCRYSTALLOGRAPHIC
COMMUNICATIONS
ISSN: 2056-9890
Volume 69| Part 10| October 2013| Pages o1563-o1564

(2E)-4-(4-Bromo­phen­yl)-2-{(2Z)-[1-(4-methyl­phen­yl)ethyl­­idene]hydrazinyl­­idene}-3-phenyl-2,3-di­hydro-1,3-thia­zole

aChemistry and Environmental Division, Manchester Metropolitan University, Manchester, M1 5GD, England, bChemistry Department, Faculty of Science, Minia University, 61519 El-Minia, Egypt, cDepartment of Physics, Faculty of Sciences, Erciyes University, 38039 Kayseri, Turkey, dDepartment of Chemistry, Tulane University, New Orleans, LA 70118, USA, and eKirkuk University, College of Science, Department of Chemistry, Kirkuk, Iraq
*Correspondence e-mail: shaabankamel@yahoo.com

(Received 11 September 2013; accepted 13 September 2013; online 18 September 2013)

In the title compound, C24H20BrN3S, the di­hydro­thia­zole ring is approximately planar, with a maximum deviation of 0.008 (2) Å, and is twisted with respect to the 4-bromo­phenyl ring, the phenyl ring and methyl­phenyl ring, making dihedral angles of 47.96 (8), 59.52 (9) and 16.96 (9)°, respectively. In the crystal, weak C—H⋯π inter­actions link inversion-related mol­ecules into supra­molecular dimers.

Related literature

For the syntheses of similar thia­zolidine compounds, see, for example: Masoudi et al. (2010[Masoudi, M., Darehkordi, A. & Moshrefi, A. (2010). World Appl. Sci. J. 10, 1313-1320.]); Darehkordia et al. (2007[Darehkordia, A., Kazem Saidib, K. & Islami, M. R. (2007). ARKIVOC, i 180-188.]) and for the synthesis of a related compound, see: Mohamed et al. (2013[Mohamed, S. K., Mague, J. T., Akkurt, M., Hassan, A. A. & Albayati, M. R. (2013). Acta Cryst. E69, o1324.]). For the range of biological activities of thia­zolidine-containing compounds, see: Pandeya et al. (1999[Pandeya, S. N., Sriram, D., Nath, G. & DeClerq, E. (1999). Eur. J. Pharm. Sci. 9, 25-31.]); Shiradkar et al. (2007[Shiradkar, M. R., Murahari, K. K., Gangadasu, H. R., Suresh, T., Kalyan, C. A., Panchal, D., Kaur, R., Burange, P., Ghogare, J., Mokale, V. & Raut, M. (2007). Bioorg. Med. Chem. 15, 3997-4008.]); Gududuru et al. (2004[Gududuru, V., Hurh, E., Dalton, J. T. & Miller, D. D. (2004). Bioorg. Med. Chem. Lett. 14, 5289-5293.]); Taranalli et al. (2009[Taranalli, A. D., Thimmaiah, N. V., Srinivas, S. & Saravanan, E. (2009). Asia. J. Pharm. Clin. Res. 2, 79-83.]); Kumar et al. (2007[Kumar, A., Rajput, C. S. & Bhati, S. K. (2007). Bioorg. Med. Chem. 15, 3089-3096.]); Rao et al. (2002[Rao, A., Carbone, A., Chimirri, A., De Clercq, E., Monforte, A. M., Monforte, P., Christophe Pannecouque, C. & Zappala, M. (2002). Il Farmaco, 57, 747-751.], 2004[Rao, A., Balzarini, J., Carbone, A., Chimirri, A., De Clercq, E., Monforte, A. M., Monforte, P., Pannecouque, C. & Zappalá, M. (2004). Il Farmaco, 59, 33-39.]); Barreca et al. (2001[Barreca, M. L., Chimirri, A., De Luca, L., Monforte, A. M., Monforte, P. A., Rao, A., Zappalà, M., Balzarini, J., De Clercq, E., Pannecouque, C. & Witvrouw, M. (2001). Bioorg. Med. Chem. Lett. 11, 1793-1796.]); Solomon et al. (2007[Solomon, V. R., Haq, W., Srivastava, K., Puri, S. K. & Katti, S. B. (2007). J. Med. Chem. 50, 394-398.]); Amin et al. (2008[Amin, K. M., Rahman, A. D. E. & Al-Eryani, Y. A. (2008). Bioorg. Med. Chem. 16, 5377-5388.]); Shih & Ying (2004[Shih, M. H. & Ying, K. F. (2004). Bioorg. Med. Chem. 12, 4633-4643.]).

[Scheme 1]

Experimental

Crystal data
  • C24H20BrN3S

  • Mr = 462.40

  • Triclinic, [P \overline 1]

  • a = 7.9622 (5) Å

  • b = 11.2672 (7) Å

  • c = 11.6370 (7) Å

  • α = 96.273 (1)°

  • β = 94.386 (1)°

  • γ = 96.302 (1)°

  • V = 1027.31 (11) Å3

  • Z = 2

  • Mo Kα radiation

  • μ = 2.12 mm−1

  • T = 150 K

  • 0.23 × 0.17 × 0.14 mm

Data collection
  • Bruker Smart APEX CCD diffractometer

  • Absorption correction: multi-scan (SADABS; Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]) Tmin = 0.60, Tmax = 0.76

  • 18958 measured reflections

  • 5310 independent reflections

  • 4582 reflections with i > 2σ(i)

  • Rint = 0.033

Refinement
  • R[F2 > 2σ(F2)] = 0.037

  • wR(F2) = 0.097

  • S = 1.09

  • 5310 reflections

  • 264 parameters

  • H-atom parameters constrained

  • Δρmax = 0.97 e Å−3

  • Δρmin = −0.52 e Å−3

Table 1
Hydrogen-bond geometry (Å, °)

Cg4 is the centroid of the C18–C23 benzene ring.

D—H⋯A D—H H⋯A DA D—H⋯A
C17—H17ACg4i 0.98 2.77 3.595 (3) 143
Symmetry code: (i) -x+3, -y, -z+2.

Data collection: APEX2 (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); cell refinement: SAINT (Bruker, 2013[Bruker (2013). APEX2, SAINT and SADABS. Bruker AXS Inc., Madison, Wisconsin, USA.]); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008[Sheldrick, G. M. (2008). Acta Cryst. A64, 112-122.]); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]); software used to prepare material for publication: WinGX (Farrugia, 2012[Farrugia, L. J. (2012). J. Appl. Cryst. 45, 849-854.]) and PLATON (Spek, 2009[Spek, A. L. (2009). Acta Cryst. D65, 148-155.]).

Supporting information


Comment top

The syntheses of a variety of thiazolidine-containing compounds have been reported (Masoudi et al., 2010; Darehkordia et al., 2007). Such compounds have been found to possess a wide range of biological properties such as antimicrobial (Pandeya et al., 1999; Shiradkar et al., 2007), antiproliferative (Gududuru et al., 2004), anti-inflammatory, analgesic, anti-ulcer (Taranalli et al., 2009; Kumar et al., 2007), anti-HIV (Rao et al., 2002; Rao et al., 2004; Barreca et al., 2001), antimalarial (Solomon et al., 2007), anticonvulsant (Amin et al., 2008) and antioxidant (Shih & Ying, 2004) activities. With this in mind and to further our ongoing study on the synthesis of various derivatives of thiazolidine compounds, we herein report the crystal structure of the title compound.

In Fig. 1, the thiazole ring (S1/N1/C1–C3) of the title compound is planar with an r.m.s. deviation of 0.002 Å. The 4-bromophenyl ring (C4–C9) makes a dihedral angle of 47.96 (8)° with the thiazole ring while the phenyl group (C10–C15) attached to the ring nitrogen makes a dihedral angle of 59.52 (9)°. The dihedral angle between the 4-methylphenyl ring (C18–C23) and the thiazole ring are 16.96 (9)°.

In the crystal, the packing consists of ribbons approximately parallel to [101] and assisted by C17—H17A···Cg4 (Cg4 is the centroid of the C18–C23 ring at 3 - x, -y, 2 - z; H17A···Cg = 2.77 Å, C17—H17A···Cg = 143°) interactions (Table 1).

Related literature top

For the syntheses of similar thiazolidine compounds, see, for example: Masoudi et al. (2010); Darehkordia et al. (2007) and for the synthesis of the title compound, see: Mohamed et al. (2013). For the range of biological activities of thiazolidine-containing compounds, see: Pandeya et al. (1999); Shiradkar et al. (2007); Gududuru et al. (2004); Taranalli et al. (2009); Kumar et al. (2007); Rao et al. (2002, 2004); Barreca et al. (2001); Solomon et al. (2007); Amin et al. (2008); Shih & Ying (2004).

Experimental top

The title compound has been prepared according to our reported method (Mohamed et al., 2013). The crude product has been crystallized from ethanol to afford translucent orange blocks suitable for X-ray diffraction (m.p.: 491 – 493 K).

Refinement top

H atoms were positioned geometrically and allowed to ride on their parent atoms with C—H = 0.95 (aromatic H) and 0.98 Å (methyl H), with Uiso(H) = 1.2Uiso(C) for aromatic H atoms and Uiso(H) = 1.5Uiso(C) for methyl H atoms.

Computing details top

Data collection: APEX2 (Bruker, 2013); cell refinement: SAINT (Bruker, 2013); data reduction: SAINT (Bruker, 2013); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEP-3 for Windows (Farrugia, 2012); software used to prepare material for publication: WinGX (Farrugia, 2012) and PLATON (Spek, 2009).

Figures top
[Figure 1] Fig. 1. View of the title compound with 50% probability ellipsoids.
[Figure 2] Fig. 2. Packing of the title compound viewed down the a-axis.
(2E)-4-(4-Bromophenyl)-2-{(2Z)-[1-(4-methylphenyl)ethylidene]hydrazinylidene}-3-phenyl-2,3-dihydro-1,3-thiazole top
Crystal data top
C24H20BrN3SZ = 2
Mr = 462.40F(000) = 472
Triclinic, P1Dx = 1.495 Mg m3
Hall symbol: -P 1Mo Kα radiation, λ = 0.71073 Å
a = 7.9622 (5) ÅCell parameters from 9928 reflections
b = 11.2672 (7) Åθ = 2.4–29.1°
c = 11.6370 (7) ŵ = 2.12 mm1
α = 96.273 (1)°T = 150 K
β = 94.386 (1)°Block, translucent orange
γ = 96.302 (1)°0.23 × 0.17 × 0.14 mm
V = 1027.31 (11) Å3
Data collection top
Bruker Smart APEX CCD
diffractometer
5310 independent reflections
Radiation source: fine-focus sealed tube4582 reflections with i > 2σ(i)
Graphite monochromatorRint = 0.033
Detector resolution: 8.3660 pixels mm-1θmax = 29.1°, θmin = 1.8°
ϕ and ω scansh = 1010
Absorption correction: multi-scan
(SADABS; Bruker, 2013)
k = 1415
Tmin = 0.60, Tmax = 0.76l = 1515
18958 measured reflections
Refinement top
Refinement on F20 restraints
Least-squares matrix: fullHydrogen site location: inferred from neighbouring sites
R[F2 > 2σ(F2)] = 0.037H-atom parameters constrained
wR(F2) = 0.097 W = 1/[Σ2(FO2) + (0.0545P)2 + 0.2353P] WHERE P = (FO2 + 2FC2)/3
S = 1.09(Δ/σ)max = 0.001
5310 reflectionsΔρmax = 0.97 e Å3
264 parametersΔρmin = 0.52 e Å3
Crystal data top
C24H20BrN3Sγ = 96.302 (1)°
Mr = 462.40V = 1027.31 (11) Å3
Triclinic, P1Z = 2
a = 7.9622 (5) ÅMo Kα radiation
b = 11.2672 (7) ŵ = 2.12 mm1
c = 11.6370 (7) ÅT = 150 K
α = 96.273 (1)°0.23 × 0.17 × 0.14 mm
β = 94.386 (1)°
Data collection top
Bruker Smart APEX CCD
diffractometer
5310 independent reflections
Absorption correction: multi-scan
(SADABS; Bruker, 2013)
4582 reflections with i > 2σ(i)
Tmin = 0.60, Tmax = 0.76Rint = 0.033
18958 measured reflections
Refinement top
R[F2 > 2σ(F2)] = 0.0370 restraints
wR(F2) = 0.097H-atom parameters constrained
S = 1.09Δρmax = 0.97 e Å3
5310 reflectionsΔρmin = 0.52 e Å3
264 parameters
Special details top

Experimental. The diffraction data were obtained from 3 sets of 400 frames, each of width 0.5° in ω, colllected at ϕ = 0.00, 90.00 and 180.00° and 2 sets of 800 frames, each of width 0.45° in ϕ, collected at ω = -30.00 and 210.00°. The scan time was 15 sec/frame.

Geometry. Bond distances, angles etc. have been calculated using the rounded fractional coordinates. All su's are estimated from the variances of the (full) variance-covariance matrix. The cell e.s.d.'s are taken into account in the estimation of distances, angles and torsion angles

Refinement. Refinement on F2 for ALL reflections except those flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F2, conventional R-factors R are based on F, with F set to zero for negative F2. The observed criterion of F2 > σ(F2) is used only for calculating -R-factor-obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F2 are statistically about twice as large as those based on F, and R-factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å2) top
xyzUiso*/Ueq
Br10.30655 (3)0.39026 (2)0.30405 (2)0.0337 (1)
S10.89651 (6)0.07711 (4)0.65607 (4)0.0232 (1)
N10.91033 (19)0.15300 (13)0.65666 (13)0.0202 (4)
N21.0854 (2)0.09850 (14)0.80890 (14)0.0249 (5)
N31.1384 (2)0.00294 (14)0.85333 (14)0.0232 (4)
C10.7740 (2)0.01832 (17)0.55032 (17)0.0236 (5)
C20.7931 (2)0.10264 (17)0.56284 (15)0.0201 (5)
C30.9789 (2)0.06878 (16)0.71838 (16)0.0209 (5)
C40.6892 (2)0.17839 (16)0.49902 (16)0.0206 (5)
C50.6570 (2)0.15626 (18)0.37854 (17)0.0235 (5)
C60.5459 (2)0.22100 (18)0.31982 (17)0.0249 (5)
C70.4664 (2)0.30698 (17)0.38211 (17)0.0231 (5)
C80.4987 (2)0.33198 (17)0.50162 (17)0.0253 (5)
C90.6109 (2)0.26850 (17)0.55927 (16)0.0227 (5)
C100.9755 (2)0.27811 (16)0.67949 (16)0.0201 (5)
C111.0510 (2)0.33501 (17)0.59380 (17)0.0235 (5)
C121.1144 (3)0.45611 (18)0.61650 (19)0.0284 (6)
C131.1018 (3)0.51860 (18)0.7235 (2)0.0306 (6)
C141.0260 (3)0.46116 (19)0.80881 (19)0.0300 (6)
C150.9628 (2)0.34014 (18)0.78762 (17)0.0248 (5)
C161.2045 (2)0.01738 (17)0.95964 (16)0.0212 (5)
C171.2183 (3)0.13675 (18)1.03341 (17)0.0272 (6)
C181.2755 (2)0.08429 (17)1.00904 (16)0.0217 (5)
C191.3742 (2)0.06595 (18)1.11581 (17)0.0257 (5)
C201.4562 (3)0.15780 (19)1.15694 (18)0.0287 (6)
C211.4419 (3)0.27080 (19)1.09447 (18)0.0283 (6)
C221.3378 (3)0.29089 (19)0.99012 (19)0.0287 (6)
C231.2561 (2)0.19953 (18)0.94795 (17)0.0258 (5)
C241.5419 (3)0.3684 (2)1.1368 (2)0.0354 (7)
H10.701600.066600.490300.0280*
H50.711300.096700.336300.0280*
H60.524800.206300.237700.0300*
H80.444500.391900.543300.0300*
H90.635100.286300.640900.0270*
H111.059600.291800.520100.0280*
H121.166500.495800.558100.0340*
H131.145200.601300.738700.0370*
H141.017100.504700.882300.0360*
H150.911700.300400.846400.0300*
H17A1.337600.171201.046700.0410*
H17B1.173300.125501.108100.0410*
H17C1.153000.191400.993600.0410*
H191.385200.010501.160900.0310*
H201.523200.142701.229300.0340*
H221.322700.368600.947200.0340*
H231.186300.215600.876800.0310*
H24A1.591100.342801.216600.0530*
H24B1.632900.381601.086400.0530*
H24C1.465800.443301.134400.0530*
Atomic displacement parameters (Å2) top
U11U22U33U12U13U23
Br10.0380 (1)0.0275 (1)0.0349 (1)0.0071 (1)0.0114 (1)0.0072 (1)
S10.0258 (2)0.0195 (2)0.0240 (2)0.0029 (2)0.0006 (2)0.0024 (2)
N10.0203 (7)0.0190 (7)0.0203 (8)0.0009 (6)0.0019 (6)0.0022 (6)
N20.0260 (8)0.0240 (8)0.0239 (8)0.0026 (6)0.0043 (6)0.0046 (6)
N30.0222 (7)0.0247 (8)0.0229 (8)0.0025 (6)0.0008 (6)0.0054 (6)
C10.0238 (9)0.0248 (9)0.0209 (9)0.0015 (7)0.0013 (7)0.0008 (7)
C20.0186 (8)0.0252 (9)0.0157 (8)0.0015 (7)0.0008 (6)0.0009 (6)
C30.0212 (8)0.0213 (8)0.0202 (9)0.0020 (7)0.0017 (7)0.0033 (7)
C40.0173 (8)0.0223 (9)0.0210 (9)0.0001 (7)0.0010 (7)0.0018 (7)
C50.0213 (8)0.0277 (9)0.0204 (9)0.0025 (7)0.0011 (7)0.0013 (7)
C60.0253 (9)0.0310 (10)0.0167 (9)0.0004 (8)0.0020 (7)0.0019 (7)
C70.0215 (8)0.0222 (9)0.0247 (9)0.0003 (7)0.0051 (7)0.0057 (7)
C80.0255 (9)0.0243 (9)0.0255 (10)0.0042 (7)0.0005 (7)0.0009 (7)
C90.0241 (9)0.0245 (9)0.0185 (9)0.0025 (7)0.0001 (7)0.0003 (7)
C100.0165 (8)0.0200 (8)0.0230 (9)0.0024 (6)0.0017 (6)0.0017 (7)
C110.0231 (9)0.0254 (9)0.0220 (9)0.0044 (7)0.0013 (7)0.0021 (7)
C120.0256 (9)0.0276 (10)0.0330 (11)0.0027 (8)0.0007 (8)0.0096 (8)
C130.0284 (10)0.0216 (9)0.0397 (12)0.0020 (8)0.0064 (9)0.0014 (8)
C140.0297 (10)0.0301 (10)0.0274 (11)0.0055 (8)0.0030 (8)0.0067 (8)
C150.0224 (9)0.0293 (10)0.0225 (9)0.0045 (7)0.0004 (7)0.0022 (7)
C160.0187 (8)0.0244 (9)0.0203 (9)0.0004 (7)0.0018 (7)0.0036 (7)
C170.0327 (10)0.0271 (10)0.0213 (10)0.0022 (8)0.0002 (8)0.0033 (7)
C180.0184 (8)0.0283 (9)0.0192 (9)0.0021 (7)0.0030 (7)0.0058 (7)
C190.0257 (9)0.0293 (10)0.0211 (9)0.0001 (7)0.0000 (7)0.0040 (7)
C200.0258 (9)0.0373 (11)0.0231 (10)0.0008 (8)0.0007 (7)0.0092 (8)
C210.0254 (9)0.0347 (11)0.0278 (11)0.0058 (8)0.0056 (8)0.0126 (8)
C220.0305 (10)0.0272 (10)0.0292 (11)0.0059 (8)0.0032 (8)0.0041 (8)
C230.0254 (9)0.0298 (10)0.0220 (9)0.0027 (8)0.0004 (7)0.0035 (7)
C240.0367 (11)0.0373 (12)0.0357 (12)0.0131 (9)0.0028 (9)0.0114 (9)
Geometric parameters (Å, º) top
Br1—C71.8966 (18)C18—C231.397 (3)
S1—C11.7439 (19)C19—C201.391 (3)
S1—C31.7573 (19)C20—C211.384 (3)
N1—C21.406 (2)C21—C221.399 (3)
N1—C31.385 (2)C21—C241.529 (3)
N1—C101.437 (2)C22—C231.390 (3)
N2—N31.398 (2)C1—H10.9500
N2—C31.290 (2)C5—H50.9500
N3—C161.293 (2)C6—H60.9500
C1—C21.345 (3)C8—H80.9500
C2—C41.471 (2)C9—H90.9500
C4—C51.396 (3)C11—H110.9500
C4—C91.401 (3)C12—H120.9500
C5—C61.393 (3)C13—H130.9500
C6—C71.384 (3)C14—H140.9500
C7—C81.387 (3)C15—H150.9500
C8—C91.383 (3)C17—H17A0.9800
C10—C111.383 (3)C17—H17B0.9800
C10—C151.387 (3)C17—H17C0.9800
C11—C121.391 (3)C19—H190.9500
C12—C131.378 (3)C20—H200.9500
C13—C141.384 (3)C22—H220.9500
C14—C151.389 (3)C23—H230.9500
C16—C171.503 (3)C24—H24A0.9800
C16—C181.483 (3)C24—H24B0.9800
C18—C191.401 (3)C24—H24C0.9800
C1—S1—C390.57 (9)C21—C22—C23121.4 (2)
C2—N1—C3113.95 (15)C18—C23—C22120.76 (18)
C2—N1—C10124.72 (15)S1—C1—H1124.00
C3—N1—C10120.74 (15)C2—C1—H1124.00
N3—N2—C3111.32 (15)C4—C5—H5120.00
N2—N3—C16114.04 (16)C6—C5—H5120.00
S1—C1—C2112.77 (14)C5—C6—H6120.00
N1—C2—C1112.72 (16)C7—C6—H6120.00
N1—C2—C4121.09 (16)C7—C8—H8120.00
C1—C2—C4125.66 (16)C9—C8—H8120.00
S1—C3—N1109.97 (12)C4—C9—H9120.00
S1—C3—N2127.42 (14)C8—C9—H9119.00
N1—C3—N2122.60 (16)C10—C11—H11120.00
C2—C4—C5120.73 (16)C12—C11—H11120.00
C2—C4—C9120.26 (16)C11—C12—H12120.00
C5—C4—C9118.85 (16)C13—C12—H12120.00
C4—C5—C6120.42 (17)C12—C13—H13120.00
C5—C6—C7119.41 (18)C14—C13—H13120.00
Br1—C7—C6119.81 (14)C13—C14—H14120.00
Br1—C7—C8118.99 (13)C15—C14—H14120.00
C6—C7—C8121.18 (17)C10—C15—H15120.00
C7—C8—C9119.13 (17)C14—C15—H15120.00
C4—C9—C8120.97 (17)C16—C17—H17A109.00
N1—C10—C11119.67 (16)C16—C17—H17B109.00
N1—C10—C15119.49 (16)C16—C17—H17C109.00
C11—C10—C15120.85 (17)H17A—C17—H17B109.00
C10—C11—C12119.43 (18)H17A—C17—H17C109.00
C11—C12—C13120.2 (2)H17B—C17—H17C109.00
C12—C13—C14120.13 (19)C18—C19—H19119.00
C13—C14—C15120.4 (2)C20—C19—H19119.00
C10—C15—C14119.06 (18)C19—C20—H20119.00
N3—C16—C17124.44 (17)C21—C20—H20119.00
N3—C16—C18116.73 (17)C21—C22—H22119.00
C17—C16—C18118.80 (16)C23—C22—H22119.00
C16—C18—C19120.75 (17)C18—C23—H23120.00
C16—C18—C23121.50 (16)C22—C23—H23120.00
C19—C18—C23117.62 (17)C21—C24—H24A109.00
C18—C19—C20121.12 (18)C21—C24—H24B109.00
C19—C20—C21121.2 (2)C21—C24—H24C109.00
C20—C21—C22117.8 (2)H24A—C24—H24B109.00
C20—C21—C24120.7 (2)H24A—C24—H24C110.00
C22—C21—C24121.52 (19)H24B—C24—H24C109.00
C1—S1—C3—N2178.97 (17)C5—C4—C9—C82.3 (3)
C3—S1—C1—C20.78 (14)C4—C5—C6—C70.5 (3)
C1—S1—C3—N10.03 (14)C5—C6—C7—Br1176.96 (14)
C3—N1—C10—C11116.25 (19)C5—C6—C7—C81.7 (3)
C3—N1—C2—C11.4 (2)C6—C7—C8—C90.8 (3)
C3—N1—C10—C1563.3 (2)Br1—C7—C8—C9177.83 (13)
C10—N1—C3—N210.2 (3)C7—C8—C9—C41.2 (3)
C10—N1—C2—C418.1 (2)N1—C10—C11—C12179.80 (17)
C10—N1—C3—S1170.78 (13)C11—C10—C15—C140.5 (3)
C2—N1—C3—N2178.25 (16)C15—C10—C11—C120.2 (3)
C3—N1—C2—C4170.66 (15)N1—C10—C15—C14179.91 (18)
C2—N1—C10—C15126.02 (18)C10—C11—C12—C130.0 (3)
C10—N1—C2—C1169.77 (16)C11—C12—C13—C140.0 (4)
C2—N1—C10—C1154.4 (2)C12—C13—C14—C150.3 (4)
C2—N1—C3—S10.81 (18)C13—C14—C15—C100.6 (3)
N3—N2—C3—S12.6 (2)N3—C16—C18—C19169.30 (16)
C3—N2—N3—C16161.26 (16)N3—C16—C18—C236.5 (2)
N3—N2—C3—N1178.52 (15)C17—C16—C18—C198.8 (2)
N2—N3—C16—C172.6 (3)C17—C16—C18—C23175.40 (17)
N2—N3—C16—C18175.39 (14)C16—C18—C19—C20173.07 (18)
S1—C1—C2—N11.38 (19)C23—C18—C19—C202.9 (3)
S1—C1—C2—C4170.28 (14)C16—C18—C23—C22173.41 (18)
N1—C2—C4—C5140.44 (17)C19—C18—C23—C222.5 (3)
C1—C2—C4—C9126.8 (2)C18—C19—C20—C210.6 (3)
C1—C2—C4—C548.6 (3)C19—C20—C21—C222.0 (3)
N1—C2—C4—C944.2 (2)C19—C20—C21—C24176.0 (2)
C2—C4—C9—C8173.15 (16)C20—C21—C22—C232.3 (3)
C2—C4—C5—C6174.01 (17)C24—C21—C22—C23175.6 (2)
C9—C4—C5—C61.4 (3)C21—C22—C23—C180.1 (3)
Hydrogen-bond geometry (Å, º) top
Cg4 is the centroid of the C18–C23 benzene ring.
D—H···AD—HH···AD···AD—H···A
C17—H17C···N20.982.282.713 (3)105
C17—H17A···Cg4i0.982.773.595 (3)143
Symmetry code: (i) x+3, y, z+2.
Hydrogen-bond geometry (Å, º) top
Cg4 is the centroid of the C18–C23 benzene ring.
D—H···AD—HH···AD···AD—H···A
C17—H17A···Cg4i0.982.773.595 (3)143
Symmetry code: (i) x+3, y, z+2.
 

Acknowledgements

The authors thank Tulane University, Manchester Metropolitan University, Erciyes University and Minia University for supporting this study.

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Volume 69| Part 10| October 2013| Pages o1563-o1564
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